Secondary metabolite: (24E)-3,4-seco-cucurbita-4,24-diene-3-hydroxy-26,29-dioic acid



(24E)-3,4-seco-cucurbita-4,24-diene-3-hydroxy-26,29-dioic acid
Summary
Molecular formula: C30H48O5
SMILES: OCCC[C@@H]1/C(=C(C(=O)O)/C)/CC[C@@H]2[C@@]1(C)CC[C@]1([C@@]2(C)CC[C@@H]1[C@@H](CC/C=C(/C(=O)O)C)C)C
InChI: InChI=1S/C30H48O5/c1-19(9-7-10-20(2)26(32)33)23-14-15-30(6)25-13-12-22(21(3)27(34)35)24(11-8-18-31)28(25,4)16-17-29(23,30)5/h10,19,23-25,31H,7-9,11-18H2,1-6H3,(H,32,33)(H,34,35)/b20-10+,22-21-/t19-,23-,24-,25-,28+,29-,30+/m1/s1
InChIKey: ATZQJRLRJKPHQB-ZECBZNPZSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
(24e)-3,4-seco-cucurbita-4,24-diene-3-hydroxy-26,29-dioic acid, 24e-3,4-seco-cucurbita-4,24-diene-3-hydroxy-26,29-dioic acid
Chemical structure download



(24E)-3,4-seco-cucurbita-4,24-diene-3-hydroxy-26,29-dioic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 488.71
Log P RDKit 6.86
Topological polar surface area (Å2) RDKit 94.83
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 24
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.8
Shape complexity RDKit 0.8
Number of rotatable bonds SwissADME 9
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3



(24E)-3,4-seco-cucurbita-4,24-diene-3-hydroxy-26,29-dioic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Number of Leadlikeness violations SwissADME 3
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.31



(24E)-3,4-seco-cucurbita-4,24-diene-3-hydroxy-26,29-dioic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.25
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes




Designed by R.P. Vivek-Ananth, M Karthikeyan and Ajaya Kumar Sahoo